"That's Life" was written by Dean Kay and Kelly Gordon and first recorded by Marion Montgomery in 1963. However, Sinatra's version remains the definitive interpretation.

: Sinatra was "pissed," and he channeled that genuine irritation into the lyrics "I've been a puppet, a pauper, a pirate, a poet...".

The album That's Life , released on , was an experimental pivot for Sinatra.

: Unlike many of his lush Nelson Riddle collaborations, this album was arranged by Ernie Freeman , who brought a bluesy, brass-heavy sound meant to compete with the rising rock and roll era.